Best Vacation Homes in Chatham
House
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
215 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
AU $420/Night
7 Nights - AU $2,942
Apartment
1 Bedroom
1 Bath
5 Guests
1399.31 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Parking
AU $315/Night
7 Nights - AU $2,207
AU $175/Night
7 Nights - AU $1,229
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
AU $265/Night
7 Nights - AU $1,852
Hotel
7.8(49 Reviews)
4 Baths
312.15 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
Air Conditioner
AU $111/Night
7 Nights - AU $775
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
172 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $469/Night
7 Nights - AU $3,285
Cottage
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $304/Night
7 Nights - AU $2,131
New
Apartment
3 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
AU $506/Night
7 Nights - AU $3,543
Chatham Luxury Rentals
Ski Chalet
9.6(38 Reviews)
7 Bedrooms
4 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
AU $2,425/Night
7 Nights - AU $16,974
House
10.0(25 Reviews)
5 Bedrooms
2 Baths
14 Guests
4000 ft²
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
AU $1,530/Night
7 Nights - AU $10,712
Villa
10.0(2 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $1,279/Night
7 Nights - AU $8,953
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $1,003/Night
7 Nights - AU $7,019
House
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $751/Night
7 Nights - AU $5,256
New
Other
4 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
AU $745/Night
7 Nights - AU $5,217
New
Ski Chalet
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Internet
- Child Friendly
Laundry
AU $697/Night
7 Nights - AU $4,877
Apartment
10.0(14 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
AU $666/Night
7 Nights - AU $4,658
Chatham Pet Friendly Vacation Rentals
Ski Chalet
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $600/Night
7 Nights - AU $4,199
House
9.8(10 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $351/Night
7 Nights - AU $2,460
House
9.4(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $389/Night
7 Nights - AU $2,723
House
4 Bedrooms
1 Bath
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $457/Night
7 Nights - AU $3,201
House
3 Bedrooms
2 Baths
8 Guests
1920 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $448/Night
7 Nights - AU $3,140
House
10.0(1 Review)
6 Bedrooms
3 Baths
12 Guests
2850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $342/Night
7 Nights - AU $2,397
House
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $1,877/Night
7 Nights - AU $13,141
House
3 Bedrooms
2 Baths
6 Guests
2700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $555/Night
7 Nights - AU $3,883
Chatham Large Vacation Homes
Other
10.0(4 Reviews)
5 Bedrooms
1 Bath
14 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
AU $559/Night
7 Nights - AU $3,913
House
4 Bedrooms
2 Baths
12 Guests
2100 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
AU $467/Night
7 Nights - AU $3,267
House
10.0(1 Review)
6 Bedrooms
6 Baths
12 Guests
6500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $1,961/Night
7 Nights - AU $13,729
Why Choose Rent By Owner for your Chatham Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chatham
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal changes in the area influence everything from outdoor activities to the serene ambiance of your vacation rental in Chatham, New York.
Peak Season Highlights
Summer (June to August)
During the summer months, the area is at its liveliest, with warm weather ideal for outdoor activities and exploring the region’s scenic beauty. This is the most popular time to secure a vacation rental, so early booking is recommended.
Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 58°F (14°C)
Fall (September to November)
This destination offers stunning autumn foliage, attracting visitors seeking vibrant colors and mild weather. Planning ahead ensures you can find the perfect vacation rentals during this picturesque season.
Average Temperature Daytime: around 65°F (18°C) - Nighttime: around 45°F (7°C)
Off-Season Highlights
Winter (December to February)
The region experiences quieter winter months with cooler temperatures, providing a peaceful retreat for those looking to enjoy cozy accommodations and scenic winter landscapes.
Average Temperature Daytime: around 35°F (2°C) - Nighttime: around 20°F (-7°C)
Early Spring (March to May)
As nature begins to awaken, this season sees fewer visitors, making it an ideal time to find deals on vacation rentals while enjoying the region’s early spring charm.
Average Temperature Daytime: around 50°F (10°C) - Nighttime: around 32°F (0°C)
Weekly Weather Forecast for Chatham
How to Book Your Chatham Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chatham
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- You can enjoy a spacious outdoor patio or deck perfect for relaxing and dining under the stars.
- Many properties feature lush, well-maintained gardens that add beauty and tranquility to your stay.
- Expect to find a private backyard ideal for outdoor activities or family gatherings.
- Some rentals offer access to scenic walking trails or nature paths nearby, allowing you to explore the area's natural beauty.
- Look for features like outdoor fire pits, perfect for cozy evenings with friends and loved ones.
- Several listings include a swimming pool, providing a refreshing way to unwind during warmer months.
- Outdoor recreational amenities such as grilling stations or picnic areas are commonly available for your convenience and enjoyment.
Top Attractions Around Chatham
What attractions are nearby?
Here, you can explore a variety of outdoor activities, cultural experiences, and scenic spots that showcase the best of the region surrounding your vacation rental in Chatham, New York.
Family Activities
- Chatham Playhouse: Enjoy a family-friendly performance or community event that captures the local arts scene, providing a memorable cultural experience for all ages.
- Olana State Historic Site: Explore the stunning landscape and historic art estate, offering engaging tours and scenic views perfect for family outings in this charming region.
- Chatham Pottery & Artisans Studio Tour: Discover local craftsmanship through guided tours and workshops that allow your family to appreciate regional artistry firsthand.
- Local Nature Trails and Parks: Spend quality time outdoors on well-maintained trails and parks that showcase the area's natural beauty, ideal for hiking, picnics, and outdoor adventures with children.
Adult Activities
- Wine Tasting Tours: Explore the local wineries in the area, where you can sample regional wines and enjoy scenic vineyard views.
- Historic Walking Tours: Discover the region’s rich history by taking guided or self-guided walks through charming streets and historic sites.
- Art Galleries & Studios: Visit the area's vibrant art scene by browsing local galleries and perhaps even participating in art workshops.
- Outdoor Recreation: Engage in activities like hiking or kayaking in nearby parks and waterways to experience the natural beauty of this destination.
Other Places to Stay in Chatham, NY
Spencertown
The Mac-Haydn Theatre
Chatham Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to discover the charming local spots and natural scenery that make this destination unique, enhancing your overall experience.
- Plan Outdoor Activities: Make the most of the region's outdoor offerings by scheduling hiking, cycling, or leisurely walks in scenic areas during your stay.
- Visit Seasonal Events: Check out any seasonal festivals or markets happening here to immerse yourself in the local culture and community atmosphere.
- Choose a Central Location: Select a vacation rental close to key points of interest to maximize convenience and reduce travel time during your visit.
Transportation Options
- Chatham Area Bus Service: This local bus service offers convenient transportation within the region, making it easy to explore the area around your vacation rental.
- Regional Train Options: Nearby train stations connect you to major cities and destinations across the region, providing a reliable travel alternative from your stay here.
- Rental Car Services: Numerous rental agencies operate in the vicinity, giving you the flexibility to explore the scenic surroundings at your own pace.
- Private Taxis and Ride-Sharing: On-demand taxi and ride-sharing services are readily available, offering a comfortable way to get around during your visit to this destination.
Local Customs Options
- Greetings and Personal Space: In this region, it is customary to greet neighbors with a friendly nod or wave, reflecting the area's welcoming community spirit.
- Local Dining Etiquette: When enjoying a meal at local eateries, you’ll find that sharing dishes and engaging in casual conversation are common practices that foster connection here.
- Seasonal Festivals and Celebrations: Participating in seasonal festivals or community events allows visitors to experience the area's rich cultural traditions firsthand.
- Respect for Nature and the Environment: The region values its natural beauty, so mindful behavior such as proper waste disposal and conservation efforts are highly regarded by residents and visitors alike.
Frequently Asked Questions About Chatham?
1. What are the top vacation rentals in Chatham?
There are a lot of options in Chatham. If you plan on staying in the Chatham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chatham:
- Gorgeous large renovated historic home on 10 acres with pool
- 2,000 sq ft loft located "downtown" with access to dining.shops.movie theater
- Modern Log Chalet - 10 acres, views, and a pond!
- BLUSH: Boutique TINY home*private spa*walk to town
- Charming 5-bedroom Vacation House in Chatham
- Chatham Cozy Country Retreat
- Sugar Shack - 300 square feet of pure sweetness.
- Serene Farmhouse Villa: Pool + Hot Tub and Grill
- It's time to FALL in Love with Upstate!
- Cozy Chatham Retreat
2. Which vacation homes in Chatham are best for families?
If you are looking for a family-friendly vacation home in Chatham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chatham:
3. How many Rentbyowner vacation rentals are available in Chatham?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 41 in the Chatham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chatham.
4. What is the cancellation policy for vacation rentals in this destination?
Cancellation policies vary by property, so it’s important to review the specific listing details. You can find this information on the rental’s page or contact the host directly for clarification.
5. How do I confirm my booking for a vacation rental in the area?
Once you select your preferred property, you can complete the booking through the listing platform. Confirmation is typically sent via email after your payment is processed, but be sure to check the property's details for any additional verification steps.
6. Are there any house rules or restrictions I should be aware of during my stay?
Each vacation rental will have its own set of house rules and restrictions, which are detailed in the listing. It’s recommended to read these carefully before confirming your reservation to ensure a smooth stay.
7. What amenities are generally included with vacation rentals here?
Most properties offer amenities such as Wi-Fi, parking, heating, and kitchen facilities. To see what’s available at a specific rental, review the listing description and photos, or contact the host directly for further details.
8. Is there local support if I encounter issues during my stay?
Hosts and property managers in the area typically provide support for any concerns during your visit. Contact information is usually available in the listing, and it’s advisable to reach out promptly if assistance is needed.
Chatham Top Rated Vacation Rentals
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
AU $426/Night
7 Nights - AU $2,983
Other
9.8(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Pool
- Ocean View
- View
- Kitchen
AU $876/Night
7 Nights - AU $6,129
House
4 Bedrooms
2 Baths
9 Guests
2414 ft²
- Hot Tub
Spa- Fireplace/Heating
- Pool
AU $1,511/Night
7 Nights - AU $10,579
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
AU $224/Night
7 Nights - AU $1,569
